RU2010143432A - METHOD FOR CRYSTALLIZING 2-AMINO-2- [2- [4- (3-BENZYloxyphenylthio) -2-Chlorophenyl] Ethyl] -1,3-Propanediol Hydrochloride - Google Patents

METHOD FOR CRYSTALLIZING 2-AMINO-2- [2- [4- (3-BENZYloxyphenylthio) -2-Chlorophenyl] Ethyl] -1,3-Propanediol Hydrochloride Download PDF

Info

Publication number
RU2010143432A
RU2010143432A RU2010143432/04A RU2010143432A RU2010143432A RU 2010143432 A RU2010143432 A RU 2010143432A RU 2010143432/04 A RU2010143432/04 A RU 2010143432/04A RU 2010143432 A RU2010143432 A RU 2010143432A RU 2010143432 A RU2010143432 A RU 2010143432A
Authority
RU
Russia
Prior art keywords
ethyl
hydrochloride
benzyloxyphenylthio
chlorophenyl
amino
Prior art date
Application number
RU2010143432/04A
Other languages
Russian (ru)
Other versions
RU2482110C2 (en
Inventor
Хидетака КОМАЦУ (JP)
Хидетака КОМАЦУ
Хироя САТОХ (JP)
Хироя САТОХ
Original Assignee
Керин Фармасьютикал Ко., Лтд. (Jp)
Керин Фармасьютикал Ко., Лтд.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Керин Фармасьютикал Ко., Лтд. (Jp), Керин Фармасьютикал Ко., Лтд. filed Critical Керин Фармасьютикал Ко., Лтд. (Jp)
Publication of RU2010143432A publication Critical patent/RU2010143432A/en
Application granted granted Critical
Publication of RU2482110C2 publication Critical patent/RU2482110C2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C07C319/28—Separation; Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1. Способ кристаллизации гидрохлорида 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола, включающий стадии: ! (1) растворения 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола в смешанном растворителе, содержащем растворитель, в котором соединение в форме его гидрохлорида имеет высокую растворимость, и растворитель, в котором гидрохлорид меньше растворим, для того, чтобы таким образом получить раствор 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола; и затем ! (2) добавления хлористоводородной кислоты к указанному выше раствору при перемешивании для того, чтобы таким образом кристаллизовать гидрохлорид 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола. ! 2. Способ по п.1, дополнительно включающий стадию (3), стадию охлаждения указанного раствора, полученного на стадии (2), при перемешивании. ! 3. Способ по п.1 или 2, где растворитель, в котором гидрохлорид соединения высоко растворим, выбран из группы, состоящей из метанола, этанола, пропилового спирта, изопропилового спирта, бутанола, трет-бутанола, ацетонитрила и пропионитрила. ! 4. Способ по п.1 или 2, где растворитель, в котором гидрохлорид соединения меньше растворим, выбран из группы, состоящей из воды, этилформиата, этилацетата, пропилацетата, этилпропионата, простого диэтилового эфира, простого диизопропилового эфира и простого диметилового эфира этиленгликоля. ! 5. Способ по п.1 или 2, где количество смешанного растворителя не меньше чем в 20 раз превышает массу указанного 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола. ! 6. Способ по п.5, где количество смешанного растворителя в 20-50 раз п� 1. The method of crystallization of 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol hydrochloride, comprising the steps of:! (1) dissolving 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol in a mixed solvent containing a solvent in which the compound in the form of its hydrochloride has a high solubility, and a solvent in which the hydrochloride is less soluble, in order to thereby obtain a solution of 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol; and then ! (2) adding hydrochloric acid to the above solution with stirring so as to crystallize 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol hydrochloride . ! 2. The method according to claim 1, further comprising a step (3), a step of cooling said solution obtained in step (2) with stirring. ! 3. The method according to claim 1 or 2, where the solvent in which the hydrochloride salt of the compound is highly soluble is selected from the group consisting of methanol, ethanol, propyl alcohol, isopropyl alcohol, butanol, tert-butanol, acetonitrile and propionitrile. ! 4. The method according to claim 1 or 2, wherein the solvent in which the hydrochloride of the compound is less soluble is selected from the group consisting of water, ethyl formate, ethyl acetate, propyl acetate, ethyl propionate, diethyl ether, diisopropyl ether and ethylene glycol dimethyl ether. ! 5. The method according to claim 1 or 2, where the amount of the mixed solvent is not less than 20 times the mass of the specified 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1, 3-propanediol. ! 6. The method according to claim 5, where the amount of mixed solvent is 20-50 times

Claims (11)

1. Способ кристаллизации гидрохлорида 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола, включающий стадии:1. The method of crystallization of hydrochloride of 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol, comprising the steps of: (1) растворения 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола в смешанном растворителе, содержащем растворитель, в котором соединение в форме его гидрохлорида имеет высокую растворимость, и растворитель, в котором гидрохлорид меньше растворим, для того, чтобы таким образом получить раствор 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола; и затем(1) dissolving 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol in a mixed solvent containing a solvent in which the compound in the form of its hydrochloride has a high solubility, and a solvent in which the hydrochloride is less soluble, in order to thereby obtain a solution of 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol; and then (2) добавления хлористоводородной кислоты к указанному выше раствору при перемешивании для того, чтобы таким образом кристаллизовать гидрохлорид 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола.(2) adding hydrochloric acid to the above solution with stirring so as to crystallize 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol hydrochloride . 2. Способ по п.1, дополнительно включающий стадию (3), стадию охлаждения указанного раствора, полученного на стадии (2), при перемешивании.2. The method according to claim 1, further comprising a step (3), a step of cooling said solution obtained in step (2) with stirring. 3. Способ по п.1 или 2, где растворитель, в котором гидрохлорид соединения высоко растворим, выбран из группы, состоящей из метанола, этанола, пропилового спирта, изопропилового спирта, бутанола, трет-бутанола, ацетонитрила и пропионитрила.3. The method according to claim 1 or 2, where the solvent in which the hydrochloride salt of the compound is highly soluble is selected from the group consisting of methanol, ethanol, propyl alcohol, isopropyl alcohol, butanol, tert-butanol, acetonitrile and propionitrile. 4. Способ по п.1 или 2, где растворитель, в котором гидрохлорид соединения меньше растворим, выбран из группы, состоящей из воды, этилформиата, этилацетата, пропилацетата, этилпропионата, простого диэтилового эфира, простого диизопропилового эфира и простого диметилового эфира этиленгликоля.4. The method according to claim 1 or 2, wherein the solvent in which the hydrochloride of the compound is less soluble is selected from the group consisting of water, ethyl formate, ethyl acetate, propyl acetate, ethyl propionate, diethyl ether, diisopropyl ether and ethylene glycol dimethyl ether. 5. Способ по п.1 или 2, где количество смешанного растворителя не меньше чем в 20 раз превышает массу указанного 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола.5. The method according to claim 1 or 2, where the amount of the mixed solvent is not less than 20 times the mass of the specified 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1, 3-propanediol. 6. Способ по п.5, где количество смешанного растворителя в 20-50 раз превышает массу указанного 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола.6. The method according to claim 5, where the amount of the mixed solvent is 20-50 times the mass of the specified 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol . 7. Способ по п.1 или 2, где растворитель, в котором высоко растворим гидрохлорид соединения, представляет собой этанол, а растворитель, в котором гидрохлорид соединения меньше растворим, представляет собой этилацетат.7. The method according to claim 1 or 2, wherein the solvent in which the compound hydrochloride is highly soluble is ethanol, and the solvent in which the compound hydrochloride is less soluble is ethyl acetate. 8. Способ по п.7, где отношение смешивания этанола к этилацетату (этанол/этилацетату) составляет 2/3.8. The method according to claim 7, where the ratio of mixing ethanol to ethyl acetate (ethanol / ethyl acetate) is 2/3. 9. Способ по п.1 или 2, где на стадии (3) кристаллизация проводится при перемешивании раствора при скорости концевой части не меньше чем 50 м/мин.9. The method according to claim 1 or 2, where in stage (3) crystallization is carried out with stirring of the solution at a speed of the end part of not less than 50 m / min. 10. Способ по п.1 или 2, где охлаждение на стадии (3) проводится при температуре в диапазоне от 0 до 30°C.10. The method according to claim 1 or 2, where the cooling in stage (3) is carried out at a temperature in the range from 0 to 30 ° C. 11. Способ получения композиции для лечении аутоиммунного заболевания, включающий введение гидрохлорида 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола, включающий стадии:11. A method of obtaining a composition for the treatment of an autoimmune disease, comprising administering 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol hydrochloride, comprising the steps of: (1) получение кристаллов гидрохлорида 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенил]этил]-1,3-пропандиола в соответствии со способом по п.1 и(1) obtaining crystals of 2-amino-2- [2- [4- (3-benzyloxyphenylthio) -2-chlorophenyl] ethyl] -1,3-propanediol hydrochloride in accordance with the method of claim 1 and (2) добавление фармацевтически приемлемого эксципиента к кристаллам, полученным на указанной выше стадии (1). (2) adding a pharmaceutically acceptable excipient to the crystals obtained in the above step (1).
RU2010143432/04A 2008-03-24 2009-03-18 Method for crystallisation of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride RU2482110C2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2008076124 2008-03-24
JP2008-076124 2008-03-24
PCT/JP2009/055235 WO2009119395A1 (en) 2008-03-24 2009-03-18 Method for crystallization of 2-amino-2-[2-[4-(3- benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride

Publications (2)

Publication Number Publication Date
RU2010143432A true RU2010143432A (en) 2012-04-27
RU2482110C2 RU2482110C2 (en) 2013-05-20

Family

ID=41113592

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2010143432/04A RU2482110C2 (en) 2008-03-24 2009-03-18 Method for crystallisation of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride

Country Status (13)

Country Link
US (2) US9493410B2 (en)
EP (2) EP3059226A1 (en)
JP (1) JP5344320B2 (en)
KR (2) KR20100127292A (en)
CN (2) CN102046594A (en)
AU (1) AU2009230269B2 (en)
BR (1) BRPI0910236A2 (en)
CA (1) CA2718987C (en)
ES (1) ES2572893T3 (en)
MX (1) MX2010010429A (en)
RU (1) RU2482110C2 (en)
TW (1) TWI429621B (en)
WO (1) WO2009119395A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009099174A1 (en) 2008-02-07 2009-08-13 Kyorin Pharmaceutical Co., Ltd. Therapeutic agent or preventive agent for inflammatory bowel disease containing amino alcohol derivative as active ingredient
CA2868252A1 (en) * 2012-04-18 2013-10-24 Kyorin Pharmaceutical Co., Ltd. 4-(3-benzyloxyphenylthio)-2-chloro-1-(3-nitropropyl)benzene crystal
IL292529A (en) 2019-10-31 2022-06-01 Idorsia Pharmaceuticals Ltd Combination of a cxcr7 antagonist with an s1p1 receptor modulator

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5475138A (en) * 1994-07-07 1995-12-12 Pharm-Eco Laboratories Incorporated Method preparing amino acid-derived diaminopropanols
DK1431284T3 (en) * 2001-09-27 2008-02-18 Kyorin Seiyaku Kk Diarylsulfide derivatives, addition salts thereof and immunosuppressants
JP4571497B2 (en) 2002-09-19 2010-10-27 杏林製薬株式会社 Amino alcohol derivatives and their addition salts and immunosuppressants
DK1602660T3 (en) * 2003-02-18 2011-05-23 Kyorin Seiyaku Kk Aminophosphonic acid derivatives, addition salts thereof, and S1P receptor modulators
CA2583846C (en) * 2004-10-12 2013-10-01 Kyorin Pharmaceutical Co., Ltd. Process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or hydrates thereof, and intermediates in the production thereof
CA2624909C (en) 2005-10-07 2013-10-01 Kyorin Pharmaceutical Co., Ltd. Therapeutic agent for treating liver disease containing 2-amino-1,3-propanediol derivative as active ingredient, and method for treating liver disease
ES2491224T3 (en) 2006-04-28 2014-09-05 Mitsubishi Tanabe Pharma Corporation 2-aminobutanol compound and its use for medical purposes

Also Published As

Publication number Publication date
KR20100127292A (en) 2010-12-03
CA2718987C (en) 2016-03-08
JPWO2009119395A1 (en) 2011-07-21
KR101767019B1 (en) 2017-08-09
EP2269982B1 (en) 2016-05-04
RU2482110C2 (en) 2013-05-20
MX2010010429A (en) 2010-11-26
EP2269982A4 (en) 2014-03-12
BRPI0910236A2 (en) 2019-09-24
US20170015624A1 (en) 2017-01-19
ES2572893T3 (en) 2016-06-02
KR20160027993A (en) 2016-03-10
TWI429621B (en) 2014-03-11
WO2009119395A1 (en) 2009-10-01
US9493410B2 (en) 2016-11-15
CN102046594A (en) 2011-05-04
TW200944495A (en) 2009-11-01
JP5344320B2 (en) 2013-11-20
EP2269982A1 (en) 2011-01-05
EP3059226A1 (en) 2016-08-24
AU2009230269A1 (en) 2009-10-01
US9920005B2 (en) 2018-03-20
CA2718987A1 (en) 2009-10-01
CN106366027A (en) 2017-02-01
AU2009230269B2 (en) 2013-02-07
US20110021636A1 (en) 2011-01-27

Similar Documents

Publication Publication Date Title
RU2018106948A (en) METHOD FOR PRODUCING SUBSTITUTED 3- (2-ANILINO-1-CYCLOGEXYL-1H-BENZIMIDAZOL-5-IL) PROPANIC ACID DERIVATIVES
JP2019052152A (en) Salts of treprostinil
CN102367253B (en) A kind of method preparing Tadalafei crystal form A
RU2010152758A (en) CRYSTALLINE FORM AND tosylate tetracycline compound CRYSTALLINE FORM AND SPECIFIED tosylate polymorph tosylate METHOD FOR PRODUCING tetracycline compound, polymorph obtained by this method, and a pharmaceutical composition based on the above crystalline forms and polymorphs
RU2007123673A (en) SUSTAINABLE CRYSTALLINE DOTAP CHLORIDE MODIFICATIONS
JP2008509953A5 (en)
JP2009507074A (en) Improved process for preparing oxazolidine protected aminodiol compounds useful as intermediates for florfenicol
MY167395A (en) Method for producing glufosinate p free acid
RU2014126351A (en) NEW TICAGRELOR CRYSTAL FORM AND METHOD FOR PRODUCING IT
RU2018145948A (en) CRYSTAL OF PYRROLOPYRIMIDINE FOR OBTAINING JAK-INHIBITOR
RU2010143432A (en) METHOD FOR CRYSTALLIZING 2-AMINO-2- [2- [4- (3-BENZYloxyphenylthio) -2-Chlorophenyl] Ethyl] -1,3-Propanediol Hydrochloride
RU2013110313A (en) AMORPHIC SOLID FORMS OF HYDROCHLORIDE 4 - [- 2 - [[5-METHYL-1- (2-NAPHTHALENYL) -1H-PYRAZOL-3-IL] OXY] ETHYL] MORPHOLINE
CN102060753A (en) Refining method of 4-phenylaminopiperidine analgesic
EP3115356A1 (en) Polymorphs of bromfenac sodium and methods for preparing bromfenec sodium ploymorphs
EA015270B1 (en) Process for the synthesis of intermediates of chloramphenicol or its analogues
CN103665063B (en) A kind of method preparing isopropyl-β-D-thiogalactoside(IPTG)
EP3021849B1 (en) Novel crystalline forms of pemetrexed tromethamine salts
RU2012122767A (en) SOME CRYSTAL HYDRATES, THEIR PHARMACEUTICAL COMPOSITIONS AND METHODS FOR PRODUCING AND USING THEM
ES2498819T3 (en) Stable crystalline salt of the (R) -3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabicyclo [2.2.2] oct-3-yl ester
AU2019349414B2 (en) Process for preparing the compound 2,2-difluoro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(S-methylsulfonimidoyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide
RU2013106503A (en) METHOD FOR OBTAINING CONTRAST AGENTS
CN104478784B (en) Crystal form of silodosin oxalate and preparation method of crystal form
EA016399B1 (en) New synthesis of substituted hydroxymethyl phenols
AR057147A1 (en) PROCEDURES TO PREPARE INTERMEDIATE COMPOUNDS OF HETEROARIL -AMINA
CN103130733B (en) Method for preparing linezolid

Legal Events

Date Code Title Description
MM4A The patent is invalid due to non-payment of fees

Effective date: 20170319